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Issue 5, 2016
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Catalytic σ-activation of carbon–carbon triple bonds: reactions of propargylic alcohols and alkynes

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Abstract

The majority reactions of alkynes in the literature are reported to proceed via either structural σ-activation or catalytic π-activation of C[triple bond, length as m-dash]C bonds. We skillfully designed novel methods for the catalytic σ-activation of C[triple bond, length as m-dash]C bonds of alkynyl compounds. For terminal alkynyl compounds, σ-activation was achieved by silver(I)-catalyzed C–H functionalization. Whereas σ-activation of internal alkynes was accomplished by the generation of propargylic cations from propargylic alcohols under Lewis-acid catalysis. These σ-activated species have been successfully used for new C–C and C–heteroatom bond formation reactions. Plausible reaction pathways were proposed based on typical control experiments to help the readers to gain insights into reactions and for further discovery of new reactions based on this concept of catalytic σ-activation of C[triple bond, length as m-dash]C bonds.

Graphical abstract: Catalytic σ-activation of carbon–carbon triple bonds: reactions of propargylic alcohols and alkynes

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Article information


Submitted
09 Oct 2015
Accepted
26 Nov 2015
First published
14 Dec 2015

Chem. Commun., 2016,52, 853-868
Article type
Feature Article
Author version available

Catalytic σ-activation of carbon–carbon triple bonds: reactions of propargylic alcohols and alkynes

R. K. Kumar and X. Bi, Chem. Commun., 2016, 52, 853
DOI: 10.1039/C5CC08386A

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